5-azido-3-pyridinecarbaldehyde | 1252800-06-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: 5-azido-3-pyridinecarbaldehyde
• 英文别名: 5-Azidopyridine-3-carbaldehyde；5-azidopyridine-3-carbaldehyde
• CAS: 1252800-06-8
• 化学式: C₆H₄N₄O
• 分子量: 148.124
• InChiKey: HICXPFQZOWXZRU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  11
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  44.3
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  吡咯 、 5-azido-3-pyridinecarbaldehyde 在 溶剂黄146 、 碳酸氢钠 作用下， 以 水 为溶剂， 反应 2.0h， 以12%的产率得到5,10,15,20-tetrakis(5-azido-3-pyridyl)porphyrin
  参考文献：
  名称：

  Facile synthesis of peptide–porphyrin conjugates: Towards artificial catalase

  摘要：

  A facile synthetic method for peptide-porphyrin conjugates containing four peptide units on one porphyrin was developed using chemoselective reactions. The key building blocks, 5,10,15,20-tetrakis(3-azidophenyl) porphyrin 1 and 5,10,15,20-tetrakis(5-azido-3-pyridyl) porphyrin 2, were efficiently synthesized and used as substrates for two well-known chemoselective reactions, traceless Staudinger ligation and copper-catalyzed azide alkyne cycloaddition (so-called click chemistry). Both reactions gave the desired compounds, and click chemistry was superior for our purpose. To confirm the value of the established methodology, nine peptide-porphyrin conjugates were synthesized, and their catalase-and peroxidase-like activity in water was evaluated. Our synthetic strategy is expected to be valuable for the preparation of artificial heme protein models. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2010.07.018
• 作为产物：
  描述：

  3-叠氮基-5-羟甲基吡啶 在 2-碘酰基苯甲酸 作用下， 以 二甲基亚砜 为溶剂， 反应 1.0h， 以96%的产率得到5-azido-3-pyridinecarbaldehyde
  参考文献：
  名称：

  Facile synthesis of peptide–porphyrin conjugates: Towards artificial catalase

  摘要：

  A facile synthetic method for peptide-porphyrin conjugates containing four peptide units on one porphyrin was developed using chemoselective reactions. The key building blocks, 5,10,15,20-tetrakis(3-azidophenyl) porphyrin 1 and 5,10,15,20-tetrakis(5-azido-3-pyridyl) porphyrin 2, were efficiently synthesized and used as substrates for two well-known chemoselective reactions, traceless Staudinger ligation and copper-catalyzed azide alkyne cycloaddition (so-called click chemistry). Both reactions gave the desired compounds, and click chemistry was superior for our purpose. To confirm the value of the established methodology, nine peptide-porphyrin conjugates were synthesized, and their catalase-and peroxidase-like activity in water was evaluated. Our synthetic strategy is expected to be valuable for the preparation of artificial heme protein models. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2010.07.018

文献信息

• Facile synthesis of peptide–porphyrin conjugates: Towards artificial catalase
  作者：Naoki Umezawa、Nobuyoshi Matsumoto、Shinsuke Iwama、Nobuki Kato、Tsunehiko Higuchi

  DOI：10.1016/j.bmc.2010.07.018

  日期：2010.9

  A facile synthetic method for peptide-porphyrin conjugates containing four peptide units on one porphyrin was developed using chemoselective reactions. The key building blocks, 5,10,15,20-tetrakis(3-azidophenyl) porphyrin 1 and 5,10,15,20-tetrakis(5-azido-3-pyridyl) porphyrin 2, were efficiently synthesized and used as substrates for two well-known chemoselective reactions, traceless Staudinger ligation and copper-catalyzed azide alkyne cycloaddition (so-called click chemistry). Both reactions gave the desired compounds, and click chemistry was superior for our purpose. To confirm the value of the established methodology, nine peptide-porphyrin conjugates were synthesized, and their catalase-and peroxidase-like activity in water was evaluated. Our synthetic strategy is expected to be valuable for the preparation of artificial heme protein models. (C) 2010 Elsevier Ltd. All rights reserved.